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Search results; Over 1,000 homes in Southold

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Guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
Studio, 2 beds, 1 private bathroom
4–9 Oct
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4.95 out of 5 average rating, 159 reviews
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Featured hotel
Hotel in Greenport
Oyster Estate, Classic king
1 bedroom, 1 king bed
4–9 Oct
New place to stay
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Featured hotel
Hotel in Bridgehampton
A Room at the Beach, Bay twin room
1 bedroom, 2 single beds
4–9 Oct
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Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
1–6 Oct
4.96 out of 5 average rating, 45 reviews
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Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms, 4 beds
17–22 Oct
5.0 out of 5 average rating, 3 reviews
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Home in East Hampton
Remarkable East Hampton Getaway with Pool
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds
11–16 Oct
4.97 out of 5 average rating, 32 reviews
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Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds
11–16 Oct
4.99 out of 5 average rating, 148 reviews
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Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds
1–8 Oct
4.95 out of 5 average rating, 37 reviews
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Top guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 64 reviews
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Guest favourite
Home in Greenport
Walk to Beach or to Town …
3 bedrooms, 4 beds
4–9 Oct
4.89 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Old Saybrook
Best of both worlds!
3 bedrooms, 4 beds
12–17 Oct
4.92 out of 5 average rating, 119 reviews
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Superhost
Home in Old Lyme
Connecticut Beach Home
Business host
10–15 Oct
New place to stay
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Home in Orient
Brand new 4 bedrm 4.5 bath home with pool & beach
4 bedrooms, 5 beds
6–11 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
3 bedrooms, 4 beds
24–29 Oct
4.98 out of 5 average rating, 172 reviews
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Luxe
Home in Montauk
Montauk modern 7-bedroom Heated Pool & hot tub
7 bedrooms, 10 beds
1–6 Nov
5.0 out of 5 average rating, 42 reviews
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Top guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds
1–6 Oct
4.98 out of 5 average rating, 169 reviews
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Top guest favourite
Room in Shelter Island
Casual Island Getaway - Walk to the Beach
1 queen bed
4–9 Oct
4.93 out of 5 average rating, 162 reviews
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Guest favourite
Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 24 reviews